Water → 1-Bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

HRID 851127Notes

Reaction equation

HRID 851127 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][F:11])=[CH:4][CH:3]=1.[Br:17]Br.O>C(Cl)Cl>[Br:17][CH:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][CH:15]=1)[C:8](=[O:14])[C:9]([CH3:12])([CH3:13])[CH2:10][F:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 221632321-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 204785111-Bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanoneYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

175 g (0.71 mol) of 1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-butan-2-one were dissolved in 500 ml of methylene chloride, and 114 g (0.71 mol) of bromine were added dropwise at 20° to 30° C., while stirring and cooling. The mixture was subsequently stirred at 20° C. for 2 hours, 200 ml of water were added carefully and the methylene chloride phase was washed several times with ice-water and dried over sodium sulphate. After distilling off the solvent in vacuo, the residue was recrystallized from cyclohexane. 180 g (78% of theory) of 1-bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-butan-2-one of melting point 73°-75° C. were obtained. ##STR26##

Workup

  1. temperaturecooling
  2. stirringThe mixture was subsequently stirred at 20° C. for 2 hours
  3. washthe methylene chloride phase was washed several times with ice-water
  4. dry with materialdried over sodium sulphate
  5. distillationAfter distilling off the solvent in vacuo
  6. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f405dd106716457099cdc6bc21344094
Source dataset
uspto-grants-1983_05
Patent number
US04382944

Reaction notes

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